Ethyl Acetate → HCID 86673826, compound

HRID 1527345Notes

Reaction equation

HRID 1527345 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13](=[O:26])[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:25])([F:24])[F:23])[CH:16]=2)[CH2:11][CH2:10][C@@H:9]1[CH2:27]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:33]=[N+:34]=[N-:35].[Na+].CCOC(C)=O.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13](=[O:26])[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:24])([F:23])[F:25])[CH:16]=2)[CH2:11][CH2:10][C@@H:9]1[CH2:27][N:33]=[N+:34]=[N-:35])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 86673825HCID 86673825, compound

Product 1

HCID 86673826HCID 86673826, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2R,5S)-2-methanesulfonyloxymethyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (465 mg, 0.97 mmol) in DMF (3 mL) was added a solution of sodium azide (313 mg, 4.82 mmol) in water (0.5 mL) and the mixture was stirred at 80° C. under nitrogen atmosphere overnight. EtOAc and a saturated aqueous solution of NaHCO3 were added, the layers were separated and the aqueous one back-extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc gradient 100:0 to 1:1) to give the desired compound. MS (LC-MS): 330 [MH−Boc]+; tR (HPLC conditions b) 5.75 min.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous one back-extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc gradient 100:0 to 1:1)

Sources & evidence

ORD record
ord-b76a261eab8a47a6b443b3144de40b6e
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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